Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions

Article Article scientifique Article Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions eng 2007 author Brinkmann Yasmin 640038 author Madhushaw Reniguntala Johnson 593117 author Jazzar Rodolphe 561371 author Bernardinelli Gérald Hugues 24765 author Kundig Ernst Peter 26401 8413-8419 10.1016/j.tet.2007.06.033 0040-4020 The synthesis of the chiral ligand (R,R)-BIPHOP-F is detailed. Its coordination to a cationic cyclopentadienyl ruthenium fragment generates [Ru (acetone)(R,R)-BIPHOP-F)Cp][SbF6], a transition metal Lewis acid that catalyzes the [3+2] dipolar cycloaddition reaction between aryl nitrile oxides and α,β-unsaturated aldehydes to give chiral 2-isoxazolines with yields of 43–98% and asymmetric purity of 60–93% ee. The stereochemistry of the major enantiomer is S, consistent with an approach of the nitrile oxide to the Cα-Si face of the enal in the anti-s-trans conformation in the catalyst site. Dewey 540 36 Département de chimie organique 141 false Tetrahedron 63 35 e62468cd-b59b-4d9c-b5ca-09562c679e4f Article Restricted file1.pdf 413913 application/pdf Vignette Public file2.jpg 16120 image/jpeg restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions	Tetrahedron			2007	723	0

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Madhushaw, Reniguntala Johnson